Reddish-blue trisazo dye.



UNITED STATES PATENT OFFICE.

HEINRICH JORDAN, or LEvEnKUsEmNEAR ooLoeun, GERMANY, Assrsuon 'ro FAR- BENFABRIKEN vonm. FRIEDR-.BAYER & 00., or ELBERFELD, GERMANY, A CORPO- RATION or GERMANY.

REDDISH-BLUE TRISAZO DYE.

No Drawing.

To all whom it may concern:

. Be it known that I, HEINRICH JORDAN,

veloped on the fiber can be obtained by first combining the dia'zo compounds of acidylpana phenylenediamins with a middle component capable of being after combination further diazotized, rediazotizing the products thusobtained, combining them with a second molecule of such middle component,

rediazotizing the aminodisazo compounds and combining the diazo bodies thus obtained with pyrazolons, suchv as methylphenyl pyrazolon, methylaryl -pyrazolon sulfonie acids, methyl-'aryl pyrazolons, naphthylpyrazolons or their sulfonic acids, methyl-pyrazolons, .pyrazolon .carboxylic acids, sulfo-aryl-pyrazolon-carboxylic acids and finally removing the acidyl group from the dyestufi's. The coloring-matters thus produced are after being dried and pulverized in the shape of their alkaline salts dark powders soluble in water; yielding upon .treatmentwith hydrosulfite and alkali para- 'phenylenediamin, one ort'wo diamins and an aminopyrazolon. They dye cotton in from. violet --to blue shades which can be diazotized and developed on the 'fiber. On developing them for instance with betanaphthol pure violet to blue shadesare obtainedof very good. fastness to washing-and to light and distinguished by the ease with which they can be discharged with hydro:

' sulfites to a pure white.

7 In order to illustrate the new process more fully the following example is given, the parts beingby weight:100- parts of -oxalyl-para-phenylenediamin are dissolved in 7000 parts of water with the addition of 65 parts of sodium carbonate and are after acidulation with 350 parts of hydrochloric acid (19 136.), diazotized at 0 to 5 C. with 69 parts of sodium nitrite; The di'azo solution is combined at 10-15 C. with a solution of 2-15 parts of the sodium salt of 1-naphthylamin-B-sulfonic acid containing 220 parts of sodium acetate (100 per cent),

Specification of Letters Patent.

Patented Aug. 8-, 1911.

' Application filed Marchc l l, 1911. Serial No. 614,395.

the combination takes place within a few minutes. The mixture is neutralized with sodium carbonate or s'oda lye, mixed with 69 parts of sodium nitrite and then diazotized by adding-at 1015 C. 1000 parts of hydrochloric acid.

The diazotation is complete after stirring the solution for 1-2 hours and the resulting diazo compound is filtered ofi, mixed with ice and water and again combined with the same qu'antity of l-naphthylamin-G-sulfonic acid in the presence-of the same quantity of sodium acetate. After stirring. the mixture for four hours, it is neutralized with caustic soda lye, cooled to 0 C. and diazotized with 69 parts of sodium nitrite and 800 parts of hydrochloric acid solution (19 Be.) The mixture is stirredfor 34 hours and the diazo compound is' then allowed to run into a solution of 174 parts of 1-phenyl-3-methylr 5-pyrazolon containing 800 parts of sodium carbonate. The dyestuff thus obtained is salted out, redissolved in 14000 parts of water and heated to boiling. 1380 parts of a 30 per cent. soda lye are added. The mixture is boiled for half an hour, diluted with cold water, neutralized with hydrochloric acid and filtered ofl. The coloring matter which has probably the following constitution:

a N IIED- is after being dried and pulverized in the The above described process is carried out in an analogous manner on using other mid dle components, such as alpha naphthyltioned end components. Of course two dif-- ferent middle components can be used instead of one compound. a

I claim -1. The herein described new trisazo dyestufis obtainable from] para -phenylenediamin, two molecules of a suitable middle component and. a yrs-zolon, which dyes are after bein drie and pulverized in the shape of t eir alkaline salts dark powders soluble in water; yielding upon reduction with hydrosulfite and alkali para-phenylenediamin, an aromatic diamin and an aminopyrazolon; dyeing cotton from violet to blue shades which can be diazotized and developed on the fiber, shades fast to washing and to light being obtained which can be disc firged with hydrosulfite to a pure white, s b'stantially as described.

2. The herein described new trisazo dyestufi obtainable from para-phenylenedicopiel of this patent may be obtained for [smut] ions In Signed and sealed this a day of October, A. 1)., 1911.

amifl, .two molecules of l-naphthylamin-G- sulfonic acid and 1-phenyl-3-methyl 5-pyrazolon, which is after being. dried and pulverized in the shape of its sodium salt a dark powder soluble in water with a bluishviolet coloration and in concentrated sulfuric acid with a green coloration, yielding upon treatmentwith hydrosulfite and alkali para-phenylenediamin, lA-diaminonaphthalene-6-sulfonic acid and 1-phenyl-3-methyl- 4-a1nino .5;pyrazolon and dyein cotton reddish-blue shades, which when iazotized on the fiberand developed with beta-naphthol change into slightly bluer shades of excelfive cents each, by addressing the "Commissioner of intents. wasnin t nc.

It ishereby certified that in Letters Patent No. 999,797, granted Augu8t 8, 1 911 upon the application of Heinrich Jordan, of Lei'erkusen, near Cologne, Germany, for an improvement in Reddish-Blue 'l risazo Dyes" errors appear in the printed specification requiring correction as followsz, Page 1, line 44, the number 100! should read 180, same page, line 88, formula, the symbol 0,11, should-read (211 and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent a B oons,

tioned end components. Of course two dif-- ferent middle components can be used instead of one compound. a

I claim -1. The herein described new trisazo dyestufis obtainable from] para -phenylenediamin, two molecules of a suitable middle component and. a yrs-zolon, which dyes are after bein drie and pulverized in the shape of t eir alkaline salts dark powders soluble in water; yielding upon reduction with hydrosulfite and alkali para-phenylenediamin, an aromatic diamin and an aminopyrazolon; dyeing cotton from violet to blue shades which can be diazotized and developed on the fiber, shades fast to washing and to light being obtained which can be disc firged with hydrosulfite to a pure white, s b'stantially as described.

2. The herein described new trisazo dyestufi obtainable from para-phenylenedicopiel of this patent may be obtained for [smut] ions In Signed and sealed this a day of October, A. 1)., 1911.

amifl, .two molecules of l-naphthylamin-G- sulfonic acid and 1-phenyl-3-methyl 5-pyrazolon, which is after being. dried and pulverized in the shape of its sodium salt a dark powder soluble in water with a bluishviolet coloration and in concentrated sulfuric acid with a green coloration, yielding upon treatmentwith hydrosulfite and alkali para-phenylenediamin, lA-diaminonaphthalene-6-sulfonic acid and 1-phenyl-3-methyl- 4-a1nino .5;pyrazolon and dyein cotton reddish-blue shades, which when iazotized on the fiberand developed with beta-naphthol change into slightly bluer shades of excelfive cents each, by addressing the "Commissioner of intents. wasnin t nc.

It ishereby certified that in Letters Patent No. 999,797, granted Augu8t 8, 1 911 upon the application of Heinrich Jordan, of Lei'erkusen, near Cologne, Germany, for an improvement in Reddish-Blue 'l risazo Dyes" errors appear in the printed specification requiring correction as followsz, Page 1, line 44, the number 100! should read 180, same page, line 88, formula, the symbol 0,11, should-read (211 and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent a B oons,

' Corrections in Letters Patent No. 999,797.

'[t is hereby certified that in Letters Patent No. 999,797, granted August 8, 1911, upon the application of Heinrich Jordan, of Lei'erkusen, near Cologne, Germany, for an improvement in Reddish-Blue Trisezo Dyes" errors appear in the printed specification requiring correction as follows:, Page 1, line 44, the number 100 1 should read 180; same page, line 86, formula, the symbol C H should read (,H 1 and that the said Let-tors Patent should be read with these corrections therein that the same may conform to the record of the ease in the Patent Office.

Signed and sealed this 3d day of October, A. D., 1911.

E. B. MOORE,

Cbmmeim'mw TM.

[SEAL] 

